Electrochemical N(sp²)–H/C(sp³)–H cross-coupling reaction between sulfoximines and alkylarenes

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5824 - 5831

Опубликована: Янв. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Язык: Английский

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Electrochemical Benzylic C–H Functionalization with Isocyanides

Organic Letters, Год журнала: 2022, Номер 24(11), С. 2125 - 2130

Опубликована: Март 14, 2022

We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)–H bonds with an isocyanide via electrochemical process giving rise to structures that are encountered in several biologically relevant compounds and drugs. This transformation proceeds under mild conditions without need for any external oxidant avoids necessity start from a prefunctionalized substrate deployment cation pool method. The anodic oxidation position subsequent addition lead formation C–C bond nitrilium hydrolyzes yield α-aryl acetamide derivatives, whereas elimination t-butyl delivers acetonitrile derivatives.

Язык: Английский

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The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

ACS Omega, Год журнала: 2022, Номер 7(44), С. 39531 - 39561

Опубликована: Окт. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Язык: Английский

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Electrochemical intramolecular N(sp²)–H/N(sp³)–H coupling for the synthesis of 1H-indazoles

Green Chemistry, Год журнала: 2023, Номер 25(10), С. 3982 - 3988

Опубликована: Янв. 1, 2023

The electrochemical intramolecular cyclization of ketimines via N–H/N–H dehydrogenation coupling has been established for the construction 1 H -indazole scaffolds.

Язык: Английский

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Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp²)–C(sp³) cross-coupling reactions

Green Chemistry, Год журнала: 2022, Номер 24(24), С. 9373 - 9401

Опубликована: Янв. 1, 2022

This review covers the recent progress in electrochemically enabled radical-mediated aryl/alkenyl C(sp 2 )–C(sp 3 ) cross-coupling reactions, including synthetic strategies, plausible mechanisms and further research outlook.

Язык: Английский

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Cyclization of Azobenzenes Via Electrochemical Oxidation Induced Benzylic Radical Generation

Organic Letters, Год журнала: 2023, Номер 25(32), С. 5978 - 5983

Опубликована: Авг. 7, 2023

An electrochemical oxidation-induced cyclization of ortho-alkyl-substituted azobenzenes has been developed. The direct benzylic C-H functionalization with respect to could proceed in the absence any catalyst or external chemical oxidant afford a number 2H-indazole derivatives moderate good yields. This protocol enables reuse byproduct same 2H-indazoles, thus significantly reducing pollution discharge synthetic chemistry.

Язык: Английский

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Electrochemical oxidation-induced benzylic C(sp³)–H functionalization towards the atom-economic synthesis of oxazole heterocycles

Green Chemistry, Год журнала: 2023, Номер 25(13), С. 5128 - 5133

Опубликована: Янв. 1, 2023

A unique electrochemical four-component reaction of terminal alkynes, (thio)xanthenes, nitriles, and water has been established in the absence any catalyst or external oxidant.

Язык: Английский

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Electrooxidation‐Induced C(sp³)–H/C(sp²)–H Radical‐Radical Cross‐Coupling between Xanthanes and Electron‐Rich Arenes

Chinese Journal of Chemistry, Год журнала: 2022, Номер 40(12), С. 1422 - 1428

Опубликована: Март 15, 2022

Comprehensive Summary The arylation of C(sp 3 ) − H bonds has been a priority research topic in organic synthesis. Minsici reactions have the powerful methods for 2 formation. Despite its mature development, scopes arenes are usually suitable electron‐deficient heterocyclic compounds, rather than electron‐rich arenes. Herein, we report an electrooxidation‐induced alkylation with evolution under exogenous oxidant‐free conditions, avoiding utilization metal catalysts. This protocol is well performed various aniline derivatives and nitrogen‐containing compounds. We anticipate that this electro‐oxidative represents important expansion classic alkylation, thereby proving attractive strategy developments radical cross‐coupling chemistry.

Язык: Английский

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Electrochemically Mediated S-Glycosylation of 1-Thiosugars with Xanthene Derivatives

Organic Letters, Год журнала: 2023, Номер 25(23), С. 4252 - 4257

Опубликована: Июнь 2, 2023

An efficient electrochemical dehydrogenative cross-coupling of benzylic C–H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various glycosylated xanthene derivatives up 91% yield. This current electrooxidative reaction characterized by high atom economy, efficiency, mild conditions, being environmentally benign, and excellent functional group tolerance. Moreover, preliminary mechanistic investigations reveal that the involves a free radical process.

Язык: Английский

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Catalyst-free benzylic C(sp³)–H cross-coupling with organotrifluoroborates enabled by electrochemistry

Green Chemistry, Год журнала: 2022, Номер 24(20), С. 7883 - 7888

Опубликована: Янв. 1, 2022

An electrochemical benzylic C(sp 3 )–H cross-coupling with organotrifluoroborates without any catalyst or external electrolyte has been developed.

Язык: Английский

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